Dimethylformamide → HCID 68778072, compound

HRID 2263074Notes

Reaction equation

HRID 2263074 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[C:13]([CH3:14])=[C:12]([NH:15][C:16]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:17])[O:11][N:10]=1.Cl[C:25]1[S:29][N:28]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:26]=1.C(N(CC)CC)C.CN(C)C=O>O>[CH3:8][C:9]1[C:13]([CH3:14])=[C:12]([NH:15][C:16]([N:18]2[CH2:19][CH2:20][N:21]([C:25]3[S:29][N:28]=[C:27]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[N:26]=3)[CH2:22][CH2:23]2)=[O:17])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 463184735-Chloro-3-(4-fluorophenyl)-1,2,4-thiadiazoleHCID 68778028N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68778072HCID 68778072, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide trifluoroacetate (210 mg, 0.621 mmol), 5-chloro-3-(4-fluorophenyl)-1,2,4-thiadiazole (133 mg, 0.621 mmol), triethylamine (0.432 ml, 3.11 mmol) and N,N-dimethylformamide (3 ml) was stirred at room temperature for 0.5 hours and the reaction mixture was poured into water. A solid was collected by filtration and recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to obtain the desired product (49.5 mg, 19.8%) as a solid.

Workup

  1. filtrationA solid was collected by filtration
  2. customrecrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-5efc2c3b391e4e29a4feb6cc35caa9c2
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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